Calixarene-based metalloporphyrins:: molecular tweezers for complexation of DABCO

被引：54
作者：
Dudic, M
Lhoták, P
Petrícková, H
Stibor, I
Lang, K
Sykora, J
机构：
[1] Prague Inst Chem Technol, Dept Organ Chem, Prague 16628 6, Czech Republic
[2] Prague Inst Chem Technol, Dept Solid State Chem, Prague 16628 6, Czech Republic
[3] ASCR, Inst Inorgan Chem, Rez 25068, Czech Republic
[4] ASCR, Inst Chem Proc Fundamentals, Prague 16502 6, Czech Republic
来源：
TETRAHEDRON | 2003年 / 59卷 / 14期
关键词：
porphyrins; calixarenes; DABCO;
D O I：
10.1016/S0040-4020(03)00290-4
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We investigated the formation of host-guest complexes between zinc porphyrins covalently attached to calixarenes via amidic bonds and a small bidentate ligand bearing two nitrogen atoms. Depending upon the calixarene structure (S vs CH2 bridges), the ligand 1,4-diazabicyclo [2.2.2] octane (DABCO) is complexed by metalloporphyrin units by two different ways. While the thiacalix[4]arene prefers an intramolecularly closed cavity with a binding constant of (1.0+/-0.1)X10(7) M-1 in CHCl3 at 294 K (stoichiometry 1:1), the classical calix[4]arene forms a complex by ligation of both porphyrin units separately (stoichiometry 2:1). The differences observed can be rationalized in terms of cavity size and the preorganization due to intramolecular hydrogen bonding of the calixarene lower rim. (C) 2003 Elsevier Science Ltd. All rights reserved.
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收藏
页码：2409 / 2415
页数：7
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